


You can call me Dee

by zation



Series: SPN Kink Bingo 2018 [16]
Category: Supernatural
Genre: Alternate Universe - College/University, Anal Sex, Awkward Conversations, Bottom Dean, Butt Plugs, Cas POV, Cas is so fucking smitten you guys, Cas is super accepting and enthusiastic, Cock Cages, Dean in Makeup, Dean in Panties, Dean in a Skirt, Dean in a wig, Dean in women's clothing, Feminization, First Time, Garter Belt, Grinding, Kissing, M/M, Past bad experiences Dean, Shy Dean Winchester, Stockings, Supernatural Kink Bingo 2018, Top Castiel
Language: English
Status: Completed
Published: 2018-08-16
Updated: 2018-08-19
Packaged: 2019-06-28 06:39:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 12,009
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15701874
Author URL: https://archiveofourown.org/users/zation/pseuds/zation
Summary: It starts with a hairpin.Or,The one where Cas notices something seemingly trivial, which leads to an embarrassed Dean eventually divulging his biggest secret, much to both of their delights.





	1. Chapter 1

**Author's Note:**

> Okay so this kink involves a number of things and can be executed in a variety of ways, I chose to do it like this and I hope you’ll like it <3
> 
>  
> 
> **Square Filled: Feminization**

 

 

The first time Cas notices something it’s very inconspicuous. He’s sitting at the back of the lecture hall, only half paying attention to Professor Cain’s philosophical rendition of Hamlet. He tends to float out into space if someone doesn’t stop him but even the preppy students at the front rows seem to have checked out. Well, it’s Friday after all and Cas supposes everyone’s just as occupied with their weekend plans as he is.

So he’s been staring out into nothingness for a while, considering his cousin Gabriel’s suggestion of that new club one town over. Clubbing isn’t really Cas’ scene but Gabe seems excited and Cas has started to find the weekly routine a bit boring of late so a change of pace might be nice.

Two rows down from him he sees Dean Winchester with his head close to his friend Charlie Bradbury as they discuss something on Charlie’s phone. It’s not that Cas is spying per se but he’s always had a thing for Dean and it’s been deepening lately, taking root the more he sees of the man. Plus, the few times he’s spoken to Charlie he’s felt as if they could be good friends and he would like more friends. Unfortunately he only shares this one class with them and Cas isn’t very good at making friends so he hasn’t bothered to pursue it. Although last time they had a group assignment Charlie had beckoned him over and he had enjoyed that. Dean had blushed very cutely on a number of occasions but Cas hadn’t had time to ask what for. He had liked it though.

Right now he’s looking at the back of Dean’s head, kind of lost in thought in general, but when the man moves away from Charlie, grinning in that way of his that makes Cas want to see him laugh even more, something catches Cas’ eye.

It’s on the top of Dean’s head, kind of, and when he moves again it seems to disappear. Cas dismisses it as a fly or something thereof and tries to focus on class. But his eyes are drawn back and he sees whatever it is on a number of occasions before Cain finally releases them. Intrigued and half expecting Dean to have something stuck in his hair, Cas makes his way down to the man before Dean can leave with Charlie.

“Dean.” He calls and the man seems to startle.

“Castiel.”

Hearing his full name in Dean’s rough voice is surprisingly pleasant and he smiles but mostly because he’s told both Dean and Charlie to call him Cas like everyone else. Charlie gives him a little salute and skips away without waiting for them. Dean looks like she abandoned him and the look is kind of cute on a grown man.

“I just wanted to tell you, I think you have something in your hair.”

“Oh?” Dean reaches up and feels around for a moment and Cas gets lost in watching Dean’s mouth pout in concentration. The man has _very_ full lips. And then Dean pulls away his hand, showing a thin hairpin. “Oh.” He breathes, suddenly blushing crimson.

“So that’s what it was.” Cas laughs. “I was just wondering, I thought maybe it was a fly or something.”

Dean looks at him with big, very round eyes, and in the next moment he bolts. Like, literally flees the room, leaving Cas extremely surprised and a bit disappointed that he didn’t get a chance to ask Dean if he wanted to join him and Gabe this weekend.

 

 

The second time is a few weeks later and in the University’s cafeteria. Cas has been thinking about that exchange in Cain’s lecture hall and somehow he thinks maybe he said something stupid. He’s wanted to talk to Dean but the man always has friends with him and Cas is not a great conversationalist so he fears he would make it worse if he got distracted by other people.

This time, though, he finds Dean alone in front of the dessert station and he hurries over with his own tray, smiling widely when the man looks up. Dean looks a bit spooked but Cas doesn’t know why so he decides to jump the hurdle anyway.

“Hi Dean.” He exclaims and watches Dean give him a small smile. “Oh those look great, do you think it’s angel cake?”

It looks like angel cake, only the frosting is pink instead of white and there's some kind of presumably edible sprinkles on top. Dean suddenly looks very anxious.

“I dunno.” He mutters gruffly and moves his tray away, going over to the sandwiches. “I don’t like sweets.”

“Really?” Cas picks the biggest piece out for himself. “My cousin owns bakery.”

“Does that mean you have to like it too?”

Well, no, Cas supposes and he can see why that information was irrelevant. He watches Dean’s hand hover over a turkey slider but he eventually picks up a meatball sub.

“I guess not but who doesn’t like cute stuff once in a while, huh?” Cas says with a wink and Dean blushes and practically runs off, leaving Cas standing there and feeling like an idiot. “Maybe he’s not interested in men.” He mutters to himself. Maybe his subpar attempts at conversation are making Dean uncomfortable? He should probably apologize about that.

 

 

The third time is at that club Gabe’s been dragging Cas to and it’s only a week after the cafeteria incident. Cas hasn’t managed to get ahold of Dean since and the only class they share had been cancelled that week because Cain’s wife was sick.

So when he sees Dean standing by a table by the side of the dance floor Cas doesn’t even hesitate to leave his cousin to his flirting. There are a lot of other people by the table too but Cas doesn’t recognize any of them and Dean is anyhow not engaged in conversation with them. He’s just standing by the table with a beer in hand, tapping the bottle and smiling slightly, looking out over the dance floor.

He startles badly when Cas slides up to him and touches his arm lightly. So badly that his beer would have spilt if Cas hadn’t been fast enough.

“Hey.” He says with a smile. Dean just stares at him. “Can we talk? Somewhere where we _can_ talk and not shout?”

Dean looks torn but he nods before Cas can consider taking back his words. They walk out the front and round a corner to the designated smoking area. There are a few people lingering there but Cas doesn’t bother with them, instead he just smiles at Dean again and to his delight the man returns a smile of his own, albeit hesitantly.

“Do you go here often?”

Dean eyes the club for a second. “Uh, no. No I just… um, a friend recommended it.”

“I got dragged here by my cousin.”

“The cousin with the bakery?”

Cas smiles widely and Dean looks strangely shy for a moment. “The same. He likes to ‘sow his oats’ or whatever.” Dean’s eyes track Cas’ hands when he make air quotes but he doesn’t comment on it like most people do. “Anyway, I just wanted to say I’m sorry if I came on a little strong before. I guess,” he laughs, feeling a little nervously if he’s honest. “I just wanted to get to know you better and I know I have a rather blunt personality so, sorry.”

Dean looks starstruck for a moment but then ducks his head, scraping his foot against the pavement as he hugs himself. “Nah, we’re good.”

“Really? That makes me very relieved, Dean.” Cas studies the other man’s face now that he’s got a chance. Dean has a very square jaw and a strangely delicate nose, sprinkled with freckles. His lashes are thicker than on some men, his cheeks are dusted with rouge, and—wait. Rouge? “Dean, are you wearing makeup?”

Dean whips his head up, looking like a deer caught in headlights so Cas assumes yes.

“N-no!” he stutters in a very unconvincing manner.

Cas smiles and feels a flutter in his chest when he notices that Dean’s normally plump lips are actually a little shiny, maybe from lip gloss? A subtle color but yes, it looks like it.

“Yes you are.” His smile widens into a grin. “It looks cute.”

What happens next is a total surprise to him. Dean grabs him by his shirt, hauls him in close only to swirl them around and slam him up against the brick wall. And not in a sexy way. He gets his face in Cas’, wondrously green eyes dark with anger.

“I ain’t wearing makeup.” He spits out in a voice so gritty it has to hurt his throat. “Don’t you fucking go ‘round telling people that. I _ain’t_ cute.”

Cas can do nothing but blink in surprise at this change in Dean’s demeanor. Dean waits half a beat before shoving Cas harder against the wall and then releasing him, stomping away. And Cas doesn’t follow him because he’s too focused on the fear he’d seen hiding under Dean’s anger.

 

 

The fourth time they talk Dean comes to find Cas. Or, well, that’s an overstatement. Actually it’s more like Dean happens to come upon Cas as he’s sitting at McDonald’s, semi-enjoying his traditional hangover meal. Not that he’s very hungover, having not been drinking the night before after his disastrous meeting with Dean but still, he had a night out and then slept horribly, he wants his sloppy burger.

Dean stops by his booth, surprise evident in his whole body and Cas can do nothing but stare up at the man for a moment before Dean looks to the side, clearly apprehensive.

“You know, um, if you want a real burger you should go to my buddy Benny’s place down on 2nd.”

Cas blinks slowly. A soggy pickle falls out of the burger he’s holding in a lax grip but he ignores it as it splatters onto the burger wrapping he’s using as a plate.

“I suppose I could say the same to you.”

“I like the strawberry shakes here.” Dean almost whispers and Cas can’t help but smile.

“Those _are_ pretty good.” He takes a bite off his burger, contemplating his next words. He wants to make amends but he doesn’t know what he keeps doing wrong. Putting his foot in his mouth, most probably because Gabe says he’s got a tendency to do that. But before he can say anything Dean slides into the booth on the other side of the table.

He looks a bit uncomfortable and kind of bothered, for the lack of a better word. Cas raises his eyebrow at the other man and Dean blushes again. He does that _a lot_ and while Cas likes it he wants to know what prompts it.

“I, um, I should apologize for…” Dean takes a deep breath, reaching to fiddle with one of the napkins Cas has spread across the table. Cas eats his burger slowly, curious to see where this is going. “I mean, I apologize Castiel.” He looks up, eyes almost sparkling and whatnot. Cas has never seen anyone’s eyes look like Dean’s do right now and he thinks it’s the most marvelous thing he’s seen. “I shouldn’t have hurt you.”

Cas nods. “Thank you, although I realize that I overstepped boundaries so I deserved getting told to stop it and you didn’t hurt me all that much, I assure you.” He smiles when Dean peeks up at him. “And I told you to call me Cas, Dean.”

Dean surprises him by smiling too. “Yeah, yeah I’d like that.”

Cas nods again and takes another bite of his burger, chewing carefully as he watches Dean tear up the napkin. Neither of them speak for a while even though Cas is burning up with the need to start a conversation.

“Did you have a good time yesterday, after we spoke?”

Dean looks to the side and shrugs. “I went home pretty soon after.”

Cas had suspected as much and he feels really bad about that. Sure, he hadn’t wanted to assume that his interference would mean so much to Dean but he had felt bad anyway. And that feeling sticks now that he sees how tired Dean looks.

“I’m sorry.”

Dean sighs and hunches in on himself, looking incredibly delicate for a man his size. “‘S not your fault, I was trying something new and I chickened out. It’s on me.”

“But it was because I called you out, wasn’t it?” Cas frowns down at his hands, burger gone now and his hands sticky with ketchup. “I seem to make you uncomfortable every time we speak and I’m sorry.”

“You… you don’t.”

Cas studies Dean’s ducked head. “You won’t even look at me now, Dean. Okay,” he sighs, pinching the bridge of his nose. Time for some real talk. “I get it that I’m coming on too strong and I’m sorry. I—well I guess I’m interested in you, in more ways than just as a friend. But I also know that that can make people uncomfortable and I _know_ that just because you have a gay friend it doesn’t make you gay, I’m not an asshole who would think something like that.” He sneers a little at himself. Dean just watches him with big eyes. “I guess what I’m trying to say is I’m sorry about coming after you, but can we please become friends anyway? I promise I won’t hit on you.”

There’s a beat of silence and then Dean makes a strangled noise, ducking his head again. “You’re not interested in me.” He croaks, making Cas frown even harder. “Stop making fun of me.”

“Making fun…?” Cas clears his throat, brow drawn tight in his confusion. “I most certainly am not.”

Dean looks spooked in that way of his and it tugs at Cas’ heart. “Shut up.”

“Dean.” Cas says, exasperated as the pieces kind of fall into place in the face of Dean’s apprehension and surprise. “Are you trying to say you’re interested in me too and you didn’t think I would like you back? That you’re surprised at this turn of events? Because if that’s the case then please say so, I’m not the best at social cues.”

Dean almost looks like he’s about to cry but then he draws a big breath, eyes closed and everything.

“Yeah.” He says after a moment, sounding more collected now. “Yeah I am and you going around talking to me as if it’s nothing _ha_ _s_ been making me nervous.”

“Why would it make you nervous?” Cas squints at Dean’s persistent blush. “Am I not supposed to talk to you when I’m trying to figure out if you could like me back? I’m not a mind reader, Dean, I need words.”

That makes Dean smile and he peeks up at Cas through his thick lashes. “Charlie said the same thing.”

“Well good.” Cas smiles too, making Dean squirm a little and oh, Cas most definitely likes seeing that.

“This whole conversation is weird, though.” Dean mumbles and Cas can do nothing but agree. He wants to blame Dean a bit because Cas has never been good at conversations but something is clearly keeping the other man back. He doesn’t say that, though.

“I agree but I’m glad we’re having it.” He reaches across the table to gently brush his fingers against Dean’s hand. “What do you say then, want to try dating me?”

“I…” Dean pulls his hand away, hunching in again. “I dunno.”

“Why not?” Cas suspects something about Dean not being out and him being afraid of homophobes or something like that but he wants to hear the man say it. “Please talk to me.”

“I’m just too weird, Cas.” Dean mumbles, his head ducked again. “I don’t think you would like me, in the end.”

Cas blinks and tries _really_ hard to understand on his own, but to no avail. “Because you like men? We’re kind of the same in that department, Dean.”

Dean grits his teeth for a moment, evident by the way the bolt in his jaw bulges and Cas kind of likes seeing it. He then looks around the McDonald’s and clearly comes to some kind of conclusion.

“Okay I’ll tell you.” He says in a low voice and stands up. “But not here.”

Not where other people can hear, Cas guesses from that and he nods, standing up as well. “Did you drive?”

“No.”

“Pity.” Cas grins as he gathers up his trash and piles it on his tray. “I love your car, sexiest there is.”

Dean makes a squeaking sound at the back of his throat but Cas ignores it in favor of throwing away his trash. He beckons Dean to follow him and the man does so silently. Outside and round the corner to the parking lot, Cas leads Dean to his beaten up Lincoln Continental and Dean smiles when he sees it.

“Charlie calls this car the Pimpmobile.”

Cas laughs and unlocks the door for Dean, holding it open. “I wish. It’s just the only piece of junk I can afford at the moment. Gets me where I want to go, though.”

Just as he’s seating himself Cas realizes that he’s got no plan on where to actually go. Dean wanted privacy for whatever it is that he wants to tell Cas and he supposes that the car offers that but at the same time the parking lot of a McDonald’s doesn’t seem like the place for a serious conversation.

So he drives them to the make-out point instead because that’s so much better.

He smiles over at Dean when he’s stopped the car and Dean returns a hesitant smile. “I didn’t take you here to assault you.”

“No I know.” Dean actually laughs a little and it makes Cas happy to hear. “You’re not that kind of guy, Cas.”

Cas feels ridiculously happy to hear that Dean thinks so. “I just wanted to go somewhere better than a parking lot and taking you home seemed too presumptuous.” He looks out the windscreen at the scenery that’s spreading out before them. “Although I see that this could be thought of as presumptuous as well.”

“It’s not.” Dean assures him.

They sit in silence for a moment, listening to the car’s engine tick as it cools down. Cas wishes he was better at small talk but at the same time he doesn’t want to disturb Dean because the other man looks like he’s gearing up to say his piece and Cas is dying to know what it is. He’d said he thought he was too weird but Cas thinks that of the two of them Dean by far seems more “normal” but besides that, who wants normalcy anyway?

 _“Not me,”_ Cas thinks as he studies Dean profile. He looks exquisite in the early morning sun and Cas wants very desperately to reach out for him. His hand, his body… make use of the purpose of this make-out point, perhaps? _“No, control yourself.”_ He chuckles to himself, unintentionally drawing Dean’s attention.

“What?”

“Nothing.” Cas says through a smile, Dean eyeing him. “I was just thinking about how gorgeous you are and how much I want to kiss you. Sorry,” he waves his hand dismissively when Dean’s eyes widen. “I explicitly told you I wouldn’t assault you and I of course won’t but I can’t help where my mind goes.”

“See, this is the thing.” Dean mumbles after a while and Cas feels bad about his behavior. He shouldn’t have said anything, clearly he’s pushing Dean’s boundaries. Again. “I wanna date you but if we do you’re gonna want to have sex.”

Hell, Cas wouldn’t say no to some hay stack tumbling right now but that’s not the point. “Dean,” he reaches over and dares take Dean’s hand in his. He smiles kindly when Dean squeezes his hand back. “We don’t have to have sex if you don’t want to. Yes, I want a romantic relationship with you and yes, that often includes sex and I would like that too but mostly I just want you, okay? We could try being romantically involved without having sex, if that’s what you want?”

Cas isn’t sure but he thinks there’s a part of the sexuality spectrum that involves this and maybe that’s where Dean land? Certainly he might fear that Cas would find that weird but he really doesn’t, “to each their own” has always been his motto.

But Dean’s shaking his head and God, Cas hopes he hasn’t put that goddamn foot in his goddamn mouth _again_.

“No, that’s not…” Dean looks at Cas with admiring eyes. “I mean, _thank you_ for saying that. It’s things like this why half the UNI is in love with you, Cas.”

“Uh…”

Dean chuckles and it’s a wonderful sound. “You really weren’t aware? Charlie said you were too dense when it came to things like that but damn, Cas, how can you not see all the pining stares?”

This is such news to Cas that he can only sit there and stare dumbly at Dean for a moment. “I really didn’t know…” perhaps because he’s only had eyes for Dean for the last year or so? He debates whether to tell the man that but Dean continues before Cas can make a decision.

“I guess not.” Dean chuckles again and then sighs, playing with Cas’ fingers absentmindedly. “Well now that you know, do you understand why I can’t wholly believe that you would wanna date someone like me?”

That sure as hell snaps Cas back to attention. “I really don’t, Dean.” He says with a frown and Dean’s brow draws tight in annoyance.

“Because you can have anyone you want, Cas.” He clarifies, looking defiantly at Cas and Cas is struggling _really_ hard to keep up with all of this. “But instead you claim that you wanna be with me, a freak who—”

“Why are you calling yourself a freak?”

“Because I like to dress up as a woman during sex, Cas!” Dean exclaims, pulling his hand from Cas’ lax grip to hunch over in the passenger seat, pressing against the door as if he’s expecting Cas to hit him. “Fuck, I didn’t wanna tell you like this but…” he draws a shuddering breath. “But last time I was interested in a guy I waited until I thought we had a stable relationship but he fucking beat me to a pulp when I told him what I wanted.”

“He _what_?” Dean jerks at Cas’ hard tone and Cas clears his throat, taking a steadying breath. “Sorry, I…” Cas’ blood is boiling but this is really not the time and hardly even his fight. “Sorry, go on.”

Dean nods slowly, eyeing Cas as if he’s waiting for him to blow up and maybe that’s not so strange, considering.

“I thought that next time a guy I like approaches me I should tell him from the beginning.” Dean mumbles in a small voice. “Better spare me the heartache. And Gordon acted like I had betrayed him or something, keeping my… my _deviancy_ a secret from him.” He draws another breath, eyes closed now and Cas’ heart aches.

“I’m so sorry, Dean.” He whispers and Dean nods. Cas grabs his arm lightly, sliding closer on the seat. “He shouldn’t have said things like that and he really shouldn’t have hit you, that’s the worst kind of violation and I…” Cas has to draw a steadying breath himself when Dean looks at him with vulnerable eyes. “I would never hurt you, Dean.”

Dean’s lower lip wobbles for a second and then he forces out a smile. “I wanna believe you but…”

“And this fantasy of yours,” Cas interrupts in a low growl, moving even closer on the seat. “Tell me all about it.”

Dean’s breathing hitches. “Wh-what?”

Cas pulls away, aware that he’s crowding Dean against the door and that it might be misinterpreted. He tries to smile as calmly as he can but his blood is still boiling, both because of this asshole of an ex-boyfriend hitting Dean and because of images of Dean in women’s underwear.

“You said ‘dress up as a woman’, what does that entail?” Dean is still looking pretty stunned and Cas likes the look on him. “Panties? Oh, you wore makeup to the club, didn’t you?” he smiles slyly. “Lipstick?”

Dean seems to unfreeze and he licks his lips slowly, definitely drawing Cas’ attention to them.

“Please don’t make fun of me.”

“I’m not.” Cas takes Dean’s hand again and the other man squeezes his hand so hard it hurts but Cas doesn’t say anything about that. “I won’t. I really want to know more. When I saw you wearing makeup last night I was…” he chuckles at himself and Dean licks his lips again. “I was so aroused, Dean. But you got mad at me and I’m sorry, obviously I brought up bad memories of this—Gordon, was it?”

“Yeah.” Dean nods slowly, looking down at their hands. “But you’re not him, not at all and I’m sorry. It’s just… that was the first time I tried showing myself in makeup out in public and you caught me by surprise. I didn’t even put on that much, I was so surprised you even saw it.”

“You said you were trying out something new.” Cas smiles when Dean looks up at him. “Was it the makeup? Were you hoping to attract someone who would like it?”

“Yeah…” Dean mumbles, eyes downcast again.

Cas jostles their joined hands until Dean meets his eyes again. “Well you did, okay? I thought you looked hot as fuck, Dean.”

Dean just stares at him for a moment before surprising Cas by laughing outright. It sounds both relieved and happy and it makes Cas’ heart soar. Oh, he’d never thought he could feel like this for another person, not since his own sad breakup a few years ago, and yes he’s been interested in getting to know Dean for a while now but he barely knows the man. And still he feels like a dog wanting to keep his master happy right now. If he had a tail he would probably be waggling it.

“You’re so fucking _different_ , Cas.” Dean laughs and Cas has been told that before and always thought of it as a compliment so he just smiles and nods. “Who the hell sees a man in their twenties wearing makeup and calls it hot?” he grins widely and Cas thinks who the hell can look at Dean and not think he’s hot? “You even called me cute yesterday, do you remember?”

“I do, it made you incredibly angry.”

Dean nods. “I’m sorry.”

“And scared.” Cas nods too when Dean just studies him. “And I see why but you don’t have to worry around me.”

“I’m starting to realize that.” Dean squeezes Cas’ hand again. “You didn’t tease me about the hairpin.”

Cas can only blink in confusion. “People’d do that?”

That makes Dean laugh. Cas is still confused because it seems so juvenile. “And the pastry.”

“I literally have no idea what you’re talking about.”

Dean grins a little teasingly. “Now who’s cute? I meant a couple of weeks ago you caught me staring at the pink and fluffy desserts, in the cafeteria. Remember?”

Cas has a vague memory of being disappointed that he had yet again managed to scare Dean off.

“Maybe…”

“You took one of those pink pastries as if it was nothing.”

“Dean,” Cas is seriously getting exasperated with his inability to understand when this is clearly important to Dean. “Words, remember?”

“We’re grown men, Cas.” Dean says in a low tone, his smile gone as he plays with Cas’ fingers again. “Grown men aren’t supposed to like stuff like that.”

Cas’ chest churns uncomfortably. “Dean, you can like whatever you want. I won’t judge you.” He slides closer again, this time putting his arm up on the backrest so that Dean ends up almost cradled against Cas’ chest. “And if that includes dressing like a woman while having sex then that’s fine by me. In fact,” he leans in so that his breath ghosts over Dean’s cheek when the other man turns to face him partially. “I wouldn’t mind _at all_.”

Dean gulps and suddenly the air in the car feels a hundred times more charged. “Even… even if it’s more than panties and makeup?”

Cas feels a sudden surge of arousal shoot through him and he grins mischievously. “Are you telling me you’d put on a dress too?”

Dean casts his eyes down, looking deliciously submissive all of a sudden. “And I have a wig too.” He whispers and Cas feels like he’s going to combust.

“I want to see that.”

Dean’s eyes this up close are like marvelous gems and Cas wishes he has a less cheesy way of describing them but for someone who’s majoring in English literature he finds himself hopelessly at a loss for words.

“Cas… I want…” Dean bites his lower lip and Cas can’t look away. God he wants to kiss the man. “I would like to show you.”

“Yes.” Cas breathes, overwhelmed by arousal. “Please, Dean. Let me see all of you, let me _support_ all of you.” He leans his forehead against Dean’s when the other man’s breathing hitches again. “And also let me be selfish in wanting to see you all dolled up for me.”

“Yeah…”

Cas is practically vibrating with the need to kiss Dean but he wants Dean completely comfortable before that and though they’re getting there he thinks it's still too soon. So close, though, Cas can practically taste the desire between them now.

“How about this? I’ll drop you off at your home and then I’ll go to mine and wash up, I’m still gross from last night and I want you to have time to prepare whatever you need to, okay?” he smiles when Dean nods slowly. “I’ll come to you again, say at three?”

“Yeah.” Dean says again, more confident this time and he smiles back. “That sounds nice.”

It sounds incredible and Cas can’t drive fast enough to Dean’s apartment. They exchange phone numbers and Dean tells him which apartment number and the code for the door before Cas drives home, high on endorphins and whatever else is making him giddy with excitement.

The truth is that he chose to postpone this not only because he thought Dean would need some preparation but also because Cas really did sleep horribly and thinks he should catch some Z’s because he wants to be able to give Dean his undivided attention. And also he didn’t shower before going to McDonald’s so that part about being gross is true…

In any case, clearly this is a sensitive issue for Dean and even though Cas wants nothing more than to devour the man he recognizes that this should be treated delicately. Dean has had some bad experiences and Cas doesn’t want to end up in that category.

Still, though, aside from how horribly Dean’s obviously been treated, Cas can’t help but think how arousing all of this is. He has to _really_ force himself not to rub one out in the shower and it’s a struggle when he keeps imaging what Dean might look like.

Yes, he’s a muscular kind of stocky man. Yes, in a way it’s probably going to look a little funny. But somehow all of that only adds to Cas’ desire. Seeing someone so clearly manly by society’s standard in obviously feminine attire feels highly arousing and Cas can’t even say why, just that he’s never thought about it before but that he can’t stop thinking about Dean in a wig right now.

He barely sleeps this time either but because of much nicer reasons. He ends up jerking off anyway, even though he wanted to save it for when or if he and Dean engage in something later tonight. But maybe it was for the best, he tries to reason as he rinses off, because it might be that Dean will just want to show him today and that they’ll just end up talking some more. Cas shouldn’t assume that they’re going to automatically have sex just because Dean said it was a sexual thing for him and besides, Cas wants a conversation too.

Yes, like this he’s more relaxed and won’t end up jumping the gun. Excited as hell, yes, but manageably so.

 

 


	2. Chapter 2

**Notes for the Chapter:**

> Thank you all so much for your wonderful support! I hope you'll like this conclusion :D

 

 

Cas calms down considerably when Dean answers the door in regular clothes. Sure, his cheeks look a bit flushed but that can easily be because of the unexpected heat wave and he’s changed into a pair of comfortable looking sweat pants but other than that he looks mostly the same as this morning.

“Hi.” He says a bit shyly and Cas smiles widely because honestly he’d take Dean however he got him.

“Hi.” He enters when Dean steps to the side to offer space. “Am I early?”

Dean eyes a wall clock by the door which professes the time to be 3:01 p.m. exactly. “Not really.” He smiles when Cas squints at the clock.

“Oh, I just thought…”

Dean hugs himself, not walking further into the apartment and Cas stays by his side, unsure if he’s even welcomed past this point. His stomach churns with the possibility that Dean has changed his mind.

“I, um,” Dean sighs and looks Cas straight in the eye. “It’s not that I don’t want to, Cas.”

Cas actually relaxes, so _that’s_ what it was. “You were scared I was pranking you.” He smiles widely but Dean doesn’t return it, clearly still apprehensive. “I’m _not_. I’m genuinely interested in you and this… well, this _kink_ for the lack of a better word.”

“It’s the appropriate word.” Dean mumbles and thankfully he seems to relax. “I’m not a transvestite, I don’t want to dress like a woman all the time or out in public in general or, I dunno, become a woman or something.”

Cas is actually unsure if those are the correct definitions of transvestites but he nods anyway. “No you said it was purely sexual.”

“Yeah.” Dean sighs and finally beckons Cas to follow him into his apartment. It’s small but seems cozy and smells like it’s been recently cleaned. Cas’ chest warms when he imagines Dean bustling about, making it nice for his visit. “I just get a kick out of having on women’s clothes and, I dunno, a guy watching me, making me do womanly stuff. Like 1950’s womanly stuff.” He smiles at Cas over his shoulder. “You know?”

Cas isn’t sure he does. “Tell me a fantasy of yours.”

Dean waves to a comfortable looking armchair and Cas sits down on it even though he’d rather sit on the couch with Dean.

“My favorite is kinda simple.” Dean mumbles, his blush spreading from his cheeks and down his chest, much to Cas’ delight. “A hot guy, maybe like you, could be sitting in that armchair and like, I dunno, reading a paper or something. You know, ignoring me. And I’d go around in something like a maid uniform, pretending to clean while I have a plug in, maybe a vibrating one that you—he could control.” Dean is looking down at his lap when he’s finished, his ears so red it looks like they’re about to catch on fire. “Or something.” He rasps and Cas is _so glad_ he masturbated before coming here.

“That,” he clears his throat when he hears how gravelly his voice is. Dean snaps his head up and Cas smiles at him. “It would be very hard to ignore you but otherwise that sounds lovely. And I would most definitely make an effort to appear to ignore you, if that’s what you want.”

“I wanna suck you off, wearing nothing but a bra and panties, while you watch the game.”

Cas’ throat constricts with want. “That would be agreeable.”

Dean smiles and it’s a bit indulgent, which for some reason revs Cas’ engine even more. “Thank you for not making fun of me.”

“That’s the third time today you’ve asked me not to mock you, am I not conveying my interest clearly enough?” Cas laughs out loud when Dean looks at him with clear surprise. “I’m sorry, that was very rude of me. But truly, Dean. I’ve never heard of a guy who got aroused from dressing like a woman and I’ve also never really considered the possibility that I could get turned on by the same. But that doesn’t mean that I don’t like what I’m hearing, and I really do. So tell me,” he leans forward, elbows on his knees as he smiles kindly at the honestly stunning man before him. “What can I do to convince you it would be okay to show me?”

“I…” Dean looks a mix between pleased and shy. “I wanna show you, I really do.”

Cas nods. “So you’ve told me and I believe you, I’m just asking—oh how about this?” he grins widely as he stands up to dig out his phone and keys from his jeans pocket. “You take this and put it somewhere I can’t see, that way you can be assured that I won’t turn into an asshole that’ll take pictures of you and also I can’t flee because this key chain has both my car keys and my apartment keys.”

“Cas, that’s too much.” Dean laughs but he stands up to accept the items when Cas reaches for him. “I believe you, we don’t have to make it complicated.”

“It’s not.” Cas assures him with a wide smile. “Like this you have the control, Dean. Maybe this whole kink of yours includes you relinquishing control in the bedroom and Lord knows I would like to mantle it for you— _with_ you, but I also want you to know you’re calling the shots right now.”

“Cas, that’s—”

Cas steps up and takes Dean’s hand in his, grabbing the man’s chin lightly with his other. “It’s not too much.” He says intimately and sees Dean swallow hard. “I want you to be comfortable around me, Dean.”

“I am.”

“I want to kiss you.”

It’s Dean who initiates the kiss and it’s absolutely glorious. Sloppy and desperate, both men hug the other so close it’s almost crushing and yet it’s somehow not close enough. Dean moans and it turns wanton when Cas snatches the man’s short hair in his hand, pulling Dean’s head to the side to deepen the kiss.

“Fuck, Cas.” Dean licks his lips, prompting Cas to kiss him again, quickly. “You’re a good kisser.”

“Can’t be anything else when I’m kissing you.” God, Cas is already fattening up in his jeans and he tries to tastefully angle his hips away from Dean’s so he won’t end up rubbing against him like a horny dog.

“You gotta stop it with the compliments.” Dean grins through a blush and Cas smiles cheekily at him.

“Why’s that? Don’t you like it?”

“I like it _too_ much.”

Holy hell, Cas wants to reach down and rub a hand against Dean’s dick, see just how much the man likes getting complimented. And with a different partner he might have but with Dean… everything just feels so special that Cas actually enjoys trying to restrain himself.

“Then you’d be interested in knowing I’ve been curious about you ever since I first saw you in Cain’s class?”

“No you haven’t.” Dean laughs nervously and Cas pulls him into a deep kiss simply because he can’t not.

His dick is definitely responding with too much enthusiasm and he feels pleasure zing through him as Dean easily yields to Cas’ kisses.

“Have you seen me dating anyone else?” he practically growls. “You’re stunning Dean, simple as that. And your mind…” he groans when he remembers the first time he’d realized that Dean was more than just a pretty face. “I regret it taking me so long to talk to you privately but that’s on me. Now you have me here, Dean, are you going to make me leave?”

“No.” Dean gasps, hands gripping Cas’ clothes tightly as if Cas had indeed tried to step back. “No, I want you.”

Cas grabs Dean’s hair again, this time craning the man’s head to the side so that he can put his lips to Dean’s heated ear.

“Then what you say you go and dress yourself in something pretty for me, princess?”

Dean’s breathing hitches in that way of his that Cas has come to love in such a short time and then he’s off, zigzagging through his living room and presumably going to his bedroom. Cas grins to himself when he hears a door slamming shut and then he sits down on the couch, one hand on his dick to try and control the situation down there.

He almost wishes he hadn’t given Dean his phone so he could have used it to distract himself but at the same time he’s proud of that decision. Judging on Dean’s previous experiences with this Cas can’t blame the man for being cautious and he wants to make sure Dean understands that Cas will do anything to make him comfortable.

Because yes, he might not understand the whole kink in itself, certainly he’d never get aroused from wearing women’s clothing, but the point is that he understands that Dean likes it. And he likes Dean, so that’s enough for him. And, truth be told, the image Dean painted for Cas just now was so goddamn arousing that Cas can’t calm down to save his life.

He looks around the room at what he can see from the couch, not one to pry or snoop but needing a distraction. He thinks he can hear running water and tries not to imagine Dean gloriously wet because that’s not helping with his dick situation. Instead he focuses on a shelf Dean has by his TV, impressively stuffed with all kinds of movies and it’s the sheer amount of different genres that pull Cas off the couch and over to the shelf.

He’s delighted to find several of his own favorite movies and he can’t wait to watch them again, preferably with Dean wrapped in Cas’ arms on this very couch. He gets lost in that little domestication fantasy for a while but jerks to attention when he hears a sound behind him.

He turns to find that Dean has once again joined him in the living room only the man looks completely transformed. Clad in a short, pleated skirt with a pink and white Scottish pattern and lace adorning the hem, he’s showing off surprisingly supple legs in sleek black stockings. He’s hugging himself and somehow he looks dainty in the black top he’s wearing. It’s without sleeves, tied together behind his neck with a delicate little string and going round his back to hug him tightly.

He looks up at Cas with big green eyes through a thin veil of soft brown hair, the wig long and straight, hair cascading down onto his shoulders. He’s clearly put on makeup as well because even though Cas has always found Dean’s eyes to be vibrant, the color stands out even more against his smoky eyeshadow, framed beautifully by lashes made thick by mascara. His cheeks are highlighted very subtly by rouge and what draws Cas’ attention the most are the way Dean has painted his lips to look even fuller, a beautiful pink to match his skirt.

He huddles against the wall for a moment, clearly uncertain whether Cas would want him to continue into the room. Cas makes the decision for him as he takes a few long strides and finds himself directly in front of Dean. The man looks at him with searching eyes and Cas can’t resist cupping Dean’s face and kissing him lightly, chastely, on his lips.

“You look stunning.” He breathes and feels a shudder go through Dean’s body. He takes a step away, taking Dean’s hand in his. “Twirl for me, baby.”

Dean spins in place, giving a surprised little sound when Cas won’t let go of his hand and Cas is mesmerized by the way the skirt lifts. From the suspenders he thought he saw there — if he’s not mistaken — Dean’s probably wearing a garter belt to match his stockings and Cas hopes to high heaven that that mean’s the man’s got on panties as well.

“Does it look alright?” Dean asks and though he doesn’t appear to try and make his voice something it’s not he’s still speaking in a softer tone, lower and more submissive and Cas’ arousal flares hot within him.

“I have no words, Dean.” Cas smiles widely. “I’ve always thought you were good-looking but this is beyond my comprehension.”

Dean squirms and Cas knows he’s laying it on thick but it’s not only to make sure Dean really understands. No, he truly feels stunned by the transformation and he doesn’t know where to even begin to properly convey that.

“You…” Dean looks down, squeezing Cas’ hand hard. “You can call me Dee.”

“Dee.” Cas growls, even though he had intended to speak like a normal human and not a beast in rut. “Such a pretty girl.” Dean gasps and looks up at Cas with big eyes, pupils slowly expanding and Cas grins at him, reaching to comb his hand through the long hair. “This looks authentic, it fits you very well.”

“It’s real hair.” Dean mumbles. “It’s from a site I got from a forum I’m a member of.”

“A forum where you can discuss things like this?” Cas guesses and Dean nods slowly.

“A friend there was the one to suggest that club.”

“I’m glad they did.” Cas murmurs intimately and Jesus Christ, he’s got to calm down but he can’t with Dean standing this close, smelling so sweetly of flowers. He leans in and sniffs, making the other man almost squeak. “Perfume?”

Dean smiles shyly. “I wanted to smell nice for you.”

“Oh Dee, baby.” Cas breathes and brushes his hands down Dean’s back. “You’re so perfect, I don’t even know where to start.”

Dean swallows hard and looks down in a way that makes Cas look down as well, following his gaze to his feet. “I wanted to wear a pair of high heels I have but that would’ve made me taller than you.”

Cas grins, thinking that Dean’s already a bit taller than him and that it’s kind of cute in this context. “I wouldn’t mind, princess.” He says sweetly. “Maybe next time you wear your heels for me, hm?”

“Yeah.” Dean half moans, half gasps and Cas likes how that sounds very much.

“Can I touch you?” he leans in when Dean nods rapidly, pressing his mouth to the man’s ear. “I probably won’t be able to stop if I start. I want to do right by you, princess, so you tell me no if you need to.”

“Please, Cas.” Dean moans, fisting Cas’ shirt tightly and Cas lets his hands drag down to the swell of the other man’s ass, grabbing his cheeks in his big hands.

It makes Dean buck forward and Cas hisses when he brushes up against Cas’ dick. “I’m a bit more excited that I had hoped to be.” He admits in a low rumble. “I want to act gentlemanly with you, Dee, but I seem to have a hard time controlling myself around you.”

Dean mewls just beautifully for him and Cas can’t resist anymore.

He slides down to his knees, sitting before Dean as he brushes his hands down the man’s legs, feeling the sleek stockings over powerful muscles under his hands in a most delicious blend. When he looks up he sees Dean biting his lower lip as he looks down at Cas. He grins up at the man, taking one of his feet in his hand and he feels a thrill when Dean allows him to place it on his knee.

“You should have on your high heels when I sit like this.” He murmurs and watches Dean’s pupils blow out. “Put me in my place, Dee.”

Dean has one hand on the wall for support and the other fisted in the short skirt. It rides up a bit and definitely shows what Cas knows is the suspender for a garter belt and he wants to get under there. He puts Dean’s foot down again, pulling on his thighs so that he stumbles closer even as Cas lets his hands slide up Dean’s legs. Up and back to his ass and he moans throatily when Cas massages the meat there.

Dean’s whole body jolts when Cas’ fingers press against his obvious lace panties to brush up against his crack and Cas is not slow to notice that. He presses Dean closer and the man leans his hands on Cas’ shoulders, gasping when Cas presses harder.

“Cas, wait…”

“What’s this, princess?” Cas murmurs, prodding the end of what’s clearly a butt plug. “Do you have a treat for me here?”

Dean moans loudly, fisting Cas’ shirt harshly. “A woman is open and ready, Cas.” He says in a hushed tone. “If she’s with a guy she likes, she’s ready so fast, I…” he looks down his body at Cas and Cas can’t help but lick his lips because he wants to kiss Dean very badly. “I wanted to be ready too, if you wanted to… to do something.”

“I want to do lots of things.” Cas groans and presses his face against Dean’s pelvis momentarily before rising to his feet. “You’re such a sweet girl for me, Dee.”

Dean fists Cas’ shirt as Cas circles the man’s slim waist with his arms, hauling him in to crush their lips together. They kiss desperately and Cas feels sharp pleasure at the thought that Dean wants this just as much as him.

“I wasn’t sure…”

“I want you.” Cas says softly, his lips brushing Dean’s as they lean against each other. “Hell I wanted you so much I had to jerk off at home or I thought I would jump you the moment you opened the door and even so here I am, jumping you.”

Dean’s breathing hitches. “I jerked off too.” He whispers, making Cas groan deeply.

“Come here, baby.” He takes Dean’s hand in his and pulls him over to the couch, sitting down and pulling so that Dean ends up straddling him. With the skirt fanned out over their laps and Dean’s sleek legs pressed against Cas’ sides he thinks this is probably the most aroused he’s ever been before the sex act in itself has even started.

Dean lets him pull on the string behind his neck and it makes half the top fall down so that Dean’s nipples are exposed. Dean makes a soft sound and Cas smiles up at him, reaching up to tuck Dean’s long hair behind his ear before he leans in and licks gently at one nipple.

“Cas!” Dean moans and grabs Cas’ hair, cradling his head to his chest.

Cas smiles to himself and laps right over the nipple, enjoying the way it perks up under his tongue, Dean’s whole body jolting. Dean is just so responsive it’s all Cas can do to keep from rutting up against the man.

“Does it feel good, princess?” Cas murmurs, rolling the swollen nub between his fingers even as he gropes Dean’s ass with his other hand. “Do you like me sucking on your titties?”

“Cas, that’s…”

“Too much?” hell, Cas doesn’t know where the line goes but he trusts Dean to tell him. It’s just occurring to him that they probably should have talked about safewords when Dean looks down at him with lust blown eyes, beautiful lips swollen from biting and kissing.

“No, I like it. Just don’t use cunt, it’s derogatory.”

Cas can’t agree more. “What about pussy?” he growls lowly, pressing on the plug and making Dean’s body jerk. “Do you want me to fuck your pretty pussy, Dee?”

Dean throws his head back, grinding against Cas’ hand and moaning loudly so yes, Cas supposes that he does and holy hell, Cas wants it too, so badly. He grabs Dean’s ass and pulls the man down as he bucks up against him, really letting Dean feel just how hard he is for him. He leans in and licks Dean’s nipple again just as the other man grabs his hair and though Cas has never really thought of hair pulling as a kink he likes it when Dean combs his fingers roughly through Cas’ thick hair as they roll together.

Frottage aside, though, Cas feels about ready to bust but he can’t feel an answering erection on Dean’s part and it’s making him slow down. No matter how much he wants Dean, this is Dean’s fantasy in the making and Cas wants to make sure the man is getting what he wants.

When he gets a hand between them he does feel something hard and it’s been pressing into his abdomen but it’s not an erection. Lifting Dean’s skirt reveals the man’s dick hopelessly trapped in a cockcage visible even through the sheer fabric of the panties he’s wearing. His dick is soft but his balls are tight and an angry shade of red. He quickly lowers the skirt again, not sure what he just saw but they’ve both stopped grinding now so he lifts it once again, getting a better look before he looks up to meet Dean’s eyes.

“What…?”

Dean’s eyes are dark with lust as he looks down at Cas. “Girls don’t have dicks to get erections with, Cas.” Dean says and his voice is so sultry Cas can barely swallow correctly. “And I knew as soon as I put this on I would get hard, the chance even higher with you looking at me. Can’t be tenting my skirt with an erection, it would shatter the illusion.”

Cas’ own dick jumps at the mental image and he wants to see it, very much, but again, this is Dean’s time. They’ll have plenty of other opportunities if Cas gets his say in this.

“Does it hurt?” he whispers huskily, fingering the cockage and feeling the intoxicating juxtaposition of the cool, hard metal and Dean’s hot, soft skin.

Dean shakes his head slowly. “I can’t get hard at all in this one so it hurts less, I think.” He swallows and juts his hips forward, brushing his caged dick harder against Cas’ hand. “Actually it feels really good.”

Cas has never had a cockcage on, hasn’t even seen one outside of amateur pornos online, but he can’t deny that it looks incredibly erotic right now. Because Dean is clearly aroused and yet he’s denying himself this one thing so he’ll appear more womanly for Cas.

It hits him hard, the realization that Dean has put so much effort and thought into this, and he loves it.

“I need to be inside you, princess.” Cas rasps, overtaken with the pure need and Dean moans.

“Here or on the bed?”

“What do you want, sweetness?” Cas kisses Dean’s chest lovingly, gently rubbing his lips across one nipple. “If it were up to me I’d take you from behind on this couch, I feel like I can’t wait.” Dean’s whole body shudders. “But how does my princess want to be taken?”

It’s clear to Cas then that while Dean gets off on being treated preciously he doesn’t actually want to be in charge. He squirms in Cas’ lap, shuddering bodily when Cas nips at his nipple. Cas’ dick is so hard it hurts and Dean’s leaking precome without even being hard.

“I have condoms in the bedroom.” Dean eventually presses out and Cas nods, grabbing Dean’s hips to help him move off Cas’ lap.

“Bedroom it is.”

Cas can’t help but admire Dean’s butt as the man leads him to his bedroom. The short skirt is swaying with the swing of Dean’s hips and Cas thinks to himself that with Dean in high heels he would be swinging his hips even more and it would look so good. His long hair flows with his movements and his perfume drifts back to Cas, making him feel high on Dean and life in general.

Dean removes his top completely as he enters the bedroom, simply pulling it over his head and the movement when he pulls his hair out of the way looks so natural that Cas just knows Dean’s had similar attires and the wig on several times. He walks up to the other man, wrapping his arms around Dean’s waist from behind and pressing in close so that Dean can feel his hard-on pressing against his ass.

“Have you let anyone else see you like this, Dee?”

Dean shakes his head slowly, rocking back against Cas’ solid frame. “After Gordon I didn’t dare…” he shakes his head again and Cas tightens his arms around Dean. “I’ve shown some of my online friends on that forum. Not my face but like, my body in outfits and stuff…”

Cas mouths along the column of Dean’s neck. “I bet they thought you looked delectable.”

Dean laughs — almost giggles. “I dunno about that. They were nice to me, though. Also,” he gets out of Cas’ embrace to turn around so they can face each other. “I’ve never shown anyone _this_ outfit.”

Cas’ body flushes hot. “I’m the first?” he growls, not really knowing why that is a turn on but definitely feeling his arousal spike at the knowledge that Dean thought he was special enough to show something he’s never shown anyone else.

“Yeah.” Dean mumbles sweetly, eyes big and sparkling. “Do you like that?”

Cas has to close his eyes for a moment, just to collect himself so he won’t end up attacking Dean despite himself.

“I don’t think I’ve ever been this aroused.” He croaks and Dean squeaks, surprising Cas by leaning in to kiss him. It’s desperate like most of their kisses have been so far but Cas wouldn’t have it any other way.

Their hands travel over the other’s body, Dean rucking up Cas’ shirt and Cas massaging Dean’s ass cheek in one hand while he plays with the man’s perky nipple with his other. Cas is so turned on and Dean keeps rubbing his caged dick against Cas’ erection.

“You’re so hard.” Dean moans coyly, sneaking a hand down to press against Cas’ poor dick. “I want it inside me.”

Cas groans and starts walking Dean towards the only bed in the room. “Are you a virgin?”

Dean laughs and it’s the most manly he’s sounded since he put on this outfit. “No. I mean, I guess Dee is, you know?” he licks his lips slowly, seductively. “But no, I’m not.”

Cas grins widely at him. “Good because I don’t know how much more I can take. I might need to be rough with you, princess.”

“Th-that’s fine.” Dean mewls, immediately reverting back to his submissive state. He sits down on the bed when they have backed up so far that the back of his knees hit it. “I want it hard in my pussy.”

Cas’ grin turns predatory and he follows Dean up the bed when the other man shimmies up to lie down with his head on the pillow. They kiss only shortly, Dean spreading his legs too wonderfully for Cas not to kiss his way down Dean’s throat, nibbling at his erratic pulse, to a dusky nipple and down his stomach.

He crouches between Dean’s legs, fingering the skirt and the soft skin underneath. “I love the skirt.” He mumbles, feeling the lace under his fingers as Dean shivers under him. “And a part of me want you to keep it on but maybe not for today?”

Dean nods and rolls to the side so that he can access a little clasp on the back. When he plucks it open and pulls down the zipper hidden in the folds of the fabric it’s almost as if the skirt splits in half. He smiles at Cas’ impressed look and then lifts his hips so that Cas easily can slid the skirt off him.

Just like Cas suspected, Dean’s wearing a garter belt and it’s absolutely beautiful on his slim waist. Dean’s thighs tremble when Cas brushes his hands up them and he can’t help but lean down and push the panties out of the way so that he can get his mouth on Dean’s dick in the cockcage. Dean whines and grabs Cas’ hair but he doesn’t push him off or tell him no so Cas takes a moment to lick the still soft dick as much as he can through the slots in the cage.

“Cas.” Dean gasps wantonly. “Oh fuck, _Cas_.”

“I want you to keep wearing the garter belt.” Cas says and his voice is so gritty with his arousal that he can barely recognize it. “When I fuck you, I want it on. And the stockings.”

Dean moans, nodding his head. “Yeah.” He pants and Cas sits back on his knees to open his jeans, relieving _some_ pressure. “Yeah I want that too. Just take off the panties, they’re not attached to the garter belt.”

Cas enjoys pulling off the panties slowly maybe more than he should, following the shape of Dean’s legs and pulling them together so that Dean has to point his toes. He captures one of Dean’s ankles in his hand, holding the foot aloft and leaning in to kiss it.

“So precious, Dee.” Cas smiles down at the man, enjoying the visage Dean makes. On his back with his light brown hair spread out around his head, his plump pink lips parted as he pants softly, gripping the comforter as he lets Cas do what he wants, Dean looks truly stunning. “Do you want to have the cockcage on while I fuck you?”

Dean takes a moment to grind his ass against the bed, obviously enjoying how the plug feels inside him. Cas has leaked so much precome that his boxers are sticky with it and he wants nothing more than to sink into Dean’s tight heat.

“I wanna get hard.” Dean eventually moans in a timid voice and Cas’ heart skips a beat. “Maybe next time I’ll keep it on?”

“Anything for my princess.” He growls and takes Dean’s hand in his only to place it on the cockcage. “I don’t know how to open it, you do that while I get a condom. And maybe some more lube?”

Dean nods and directs Cas to the nightstand with a single look. “Take a condom for me too.” He says in a low whisper. “So there’s less mess.”

Because women typically don’t come like a man does, Cas suspects but doesn’t say because he’s fine with it either way as long as Dean is satisfied and enjoys this. And judging by how the man’s dick starts to fill out all on its own as soon as he’s gotten the cage off Cas would say that Dean is enjoying it very much.

He moans and thumbs the base of his dick but seems to not want to stroke it too much and when Cas starts to pull down his pants, Dean reaches out to stop him instead.

“Keep your clothes on?” he mumbles shyly and Cas doesn’t see why not so he just climbs on the bed again, only pulling out his dick and rolling on a condom.

“Do you not want to see me naked or do you like it better like this?”

Dean looks up sharply. “I wanna see you naked like nothing else, Cas.” He says earnestly and Cas smiles to himself, getting in position to pull out the plug from Dean’s puffy rim. “It’s just… part of the fantasy, I guess…”

“You don’t have to explain.” Cas grins, fingering the plug, which makes Dean spread his legs again and arch his back. “I was just teasing you. If my baby doll wants me to take her with such heat that I can’t even bother to take off my own clothes then that’s what she’ll get.”

Dean’s dick quivers, hardening fully as a clear pearl of precome bubbles up at the head. Cas watches with satisfaction how Dean’s balls pull tight when he tugs at the plug. He’s honestly never wanted anyone this much before and he can feel his own balls drawing tight as well.

“Cas, I need you.” Dean moans, high-pitched as the plug slips free with a beautiful sound. Cas pours lube directly on Dean’s hole and pushes it inside with two fingers, spreading the lube and testing the give as Dean moans again, fucking himself on Cas’ fingers.

“This is going to be fast and dirty, princess.” Cas growls. “So close to blowing just from this.”

“Oh _fuck_.” Dean grunts, the words punched out of him as he reaches down and rolls on a condom of his own, stroking his dick with quick little flicks of his wrist. “Get inside me, Cas. I need it so fucking much, need you to fuck me hard, fuck me into the mattress.” He grunts again when Cas grabs his thighs and all but pulls him into the thrust that pushes Cas inside him, almost to the hilt in one go.

They pause for the slightest of moments, just kind of panting into the shared space between them, and then Cas pulls out again. He goes slowly, getting his knees under him and collecting himself from the initial pulse of pleasure that shot through him as he entered Dean’s tight hole. He feels almost shaky and as he pushes inside again Dean clenches down on him, tight as a vice, and Cas groans deeply.

His dick is hard as iron as he starts really fucking Dean and good Lord, Dean’s body is so _hot_. So soft and warm and so perfect for him to just sink into again and again. He doesn’t even try to kiss Dean right now, instead just mouthing at the man’s clavicle as he holds him still by his hips. Dean has wrapped his legs around Cas as best as he can and Cas wishes that he could feel the stockings against his skin but also can’t deny how hot it is that he’s just pulled his dick out of his boxers and Dean’s almost naked. It makes the act gritty and sexy and Cas can’t stop himself from pounding hard into Dean.

Dean is gripping him tightly, panting and moaning loudly and Cas loves how desperate he sounds. His dick is a hard line against Cas’ stomach, getting rubbed mercilessly against Cas’ shirt and Cas wants to take him in hand but at the same time he wants Dean to come on his dick alone. With that in mind he shifts his grip, angling Dean’s hips in a way he hopes will make him find his mark and he growls in triumph when Dean wails and clamps down on him.

“Fuck me there, Cas!” he near screams and Cas grins to himself, face smashed against Dean’s chest as he fucks the man with short and powerful thrusts, each apparently hitting the man’s sweet spot if Dean’s continued string of babbling is something to go on.

Cas’ own orgasm is building beyond his control and he feels it like a living thing inside him. Like a caged beast, thrashing against its prison and God, he wants to let it out so badly. And he’s going to, so soon.

“God, I need you to come, Dee.” He groans, lapping his way up to Dean’s open mouth. “You have to come for me, princess. Come on my cock like a good girl.”

“Yeah, Cas. Yeah.” Dean whines, grabbing Cas’ hair and holding him as they kiss messily.

Cas presses his body down harder against Dean, rubbing up against the man’s hard dick with every thrust. Dean sobs out a broken moan and fucks himself into Cas’ thrusts, his whole body convulsing as he comes hard. He shakes and gasps in Cas’ arms and the way his tight hole spasms around Cas’ dick makes Cas go off like a rocket. He comes so hard he’s almost certain the force of it ripped open the condom and he can’t get a single sound out for way too long.

When he eventually gets his bearings back he draws a big breath and all but collapses down on Dean, dick still pretty hard and lodged inside the other man.

“Cas.” Dean says after a moment and Cas rises to his elbows quickly, sure he’s crushed him.

“Sorry.”

“No,” Dean laughs and Cas smiles down at him, thinking the man’s never looked so beautiful before. Face all flushed from sex and the long hair framing his face. “I was just gonna say that that was fucking awesome.”

“It was.” Cas agrees and sits up on his knees, grinding his dick inside Dean and making the man gasp a little in surprise. “It _is_.”

“You’re still hard.” Dean laughs, grin wide and spectacular. “I love that.”

Cas is starting to think that he might love Dean, period. “Might be that I have another go in me.”

Dean’s eyebrows shoot to his hairline. “For real?”

Cas grinds his hips in a slow figure eight, enjoying the pinpricks of pleasure that go through him, so sharp they’re _almost_ painful, dancing on that thin line just perfectly.

“I don’t know, it’s never happened before.” He grins at Dean, suddenly feeing boyishly happy. “Then again, I’ve never had sex with someone who’s simultaneously a hot as fuck man and a beautifully demure woman before either. Maybe you woke a beast in me.”

Dean blinks for a moment before bursting out laughing, which makes his hole clench rhythmically around Cas’ _very_ interested dick.

“I knew I made a good choice falling in love with you, Cas.” Dean grins through actual tears and Cas’ chest feels like it’s going to explode. “You really do accept this side of me, don’t you?”

Cas’ interest is piqued about the “falling in love” part but he decides to circle back to that later. Instead he just drapes his body over Dean’s, pulling him in tightly and kissing him lovingly.

“I accept you, Dean. And I want to do it all with you. Have sex with you dressed as a woman, or dressed as a man, indulging in all your fantasies.” He grins when he sees on Dean’s face how much that means to the man. “But also date you for real. Talk about the class we share and classes we don’t share, meet each other’s friends, maybe watch a movie? I saw you have _Rogue One_ , I’ve yet to see that one and I would very much like to cuddle on the couch with you.”

“Are you asking me to Netflix and chill with you?” Dean grins and Cas’ dick jumps inside the man at the beautiful sight and the pure relief and want in Dean’s tone.

“In a moment.” Cas growls playfully. “Just have to take care of my dick situation first.”

“Take off your clothes.” Dean mumbles, still grinning. “I wanna see if you’re as hot as I think you are.”

“Well then,” Cas gets up on his knees again, even if that makes his dick slide out a bit, and starts unbuttoning his shirt. “Prepare to be amazed, princess.”

Dean laughs again and Cas would be hard-pressed to choose which one is better; the sound or the feeling of Dean yet again clenching around Cas’ dick. His dick wins out this time but Dean will give him many more opportunities to enjoy everything else as well, in their future together.

 

 

 

**Notes for the Chapter:**

> Okay so someone asked for a pic to represent how Dean looks in his wig and I found [this](http://img15.deviantart.net/71da/i/2012/177/0/7/what_if_rhaegar_were_played_by_jensen_ackles_by_marinavictoria-d54wn8d.png), which I thought was absolutely perfect! I mean, the color is supposed to much darker but otherwise it's spot-on for what I had in mind! (actually that’s Jensen Ackles as Rhaegar Targaryen by [MarinaSchiffer](https://marinaschiffer.deviantart.com/gallery/?rnrd=110113) on Deviantart :D)
> 
> Also, are you telling me [this](https://i.pinimg.com/736x/ce/97/b3/ce97b395077de4ed3862d858f867b014--tartan-mini-skirt-lingerie-for-men.jpg) isn’t sexy as fuck?! (warning: kinda NSFW I guess lol)


End file.
